Triethylamine → 5-Bromo-3-(2-chloro-ethyl)-thiophene-2-carboxylic acid [4-((R)-3-dimethylamino-pyrrolidin-1-yl)-phenyl]-amide

HRID 69504Notes

Reaction equation

HRID 69504 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([N:13]([CH3:15])[CH3:14])[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:23][C:24]1[S:28][C:27]([C:29](Cl)=[O:30])=[C:26]([CH2:32][CH2:33][Cl:34])[CH:25]=1>C1COCC1>[CH3:14][N:13]([CH3:15])[C@@H:10]1[CH2:11][CH2:12][N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:29]([C:27]3[S:28][C:24]([Br:23])=[CH:25][C:26]=3[CH2:32][CH2:33][Cl:34])=[O:30])=[CH:3][CH:4]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59815627[(R)-1-(4-aminophenyl)pyrrolidin-3-yl]dimethylamineHCID 866351075-Bromo-3-(2-chloro-ethyl)-thiophene-2-carbonyl chloride

Product 1

HCID 866351065-Bromo-3-(2-chloro-ethyl)-thiophene-2-carboxylic acid [4-((R)-3-dimethylamino-pyrrolidin-1-yl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of [(R)-1-(4-Amino-phenyl)-pyrrolidin-3-yl]-dimethyl-amine (349 mg) and triethylamine (0.25 mL) in THF (4 mL) a solution of 5-Bromo-3-(2-chloro-ethyl)-thiophene-2-carbonyl chloride (489.6 mg) in THF (3 mL) added dropwise. The mixture was stirred for 2 h at room temperature. Then the solvent was removed in vacuum and then water and ethyl acetate were added to the residue. The aqueous phase was extracted with ethyl acetate three times. The combined organic phases were dried over sodium sulfate and the solvent was removed in vacuum. In this way the product was obtained with molecular weight 456.84 (C19H23BrClN3OS); MS (ESI): 456, 458 (M+H+).

Workup

  1. additionadded dropwise
  2. customThen the solvent was removed in vacuum
  3. additionwater and ethyl acetate were added to the residue
  4. extractionThe aqueous phase was extracted with ethyl acetate three times
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customthe solvent was removed in vacuum
  7. customIn this way the product was obtained with molecular weight 456.84 (C19H23BrClN3OS)

Sources & evidence

ORD record
ord-fd047b3982ac48afb0bff700461f8660
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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